- Synthesis of new cellulose ethers using Suzuki-Miyaura reactions
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Cellulose ethers are functionalized biopolymers that are industrially produced through drastic conditions employing gaseous reactants with a high risk of industrial accident. The cellulose ethers that are commercially available generally bear short carbon-chains. In this work, an alternative method using non-gaseous chemicals is proposed. It relies on the use of the Suzuki-Miyaura reaction employing mild, moisture- and air-stable conditions. Relatively innocuous reagents are used for this step, which allows the formation of a wide range of cellulose ethers bearing various functional groups with different chain-length.
- Goncalves, Cédric,Favre, Camille,Feuardant, Pierre,Klein, Sarah,Vaca-Garcia, Carlos,Cecutti, Christine,Thiébaud-Roux, Sophie,Vedrenne, Emeline
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Read Online
- Preparation and characterization of inclusion complex of carbosilane dendrimers and cyclodextrins
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In this paper, 1st-4th generation of carbosilane dendrimers [G 1(PhBr)-G4(PhBr)] were synthesized with bromophenyl group as a core molecule. Then, the inclusion reaction of α-, β-, γ-cyclodextrin and four generations of carbosilane d
- Zhu, Lin,Liu, Huashi,Guan, Ruifang,Zhou, Chuanjian
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Read Online
- Catalytic, contra-Thermodynamic Positional Alkene Isomerization
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The positional isomerization of C═C double bonds is a powerful strategy for the interconversion of alkene regioisomers. However, existing methods provide access to thermodynamically more stable isomers from less stable starting materials. Here, we report
- Occhialini, Gino,Palani, Vignesh,Wendlandt, Alison E.
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supporting information
p. 145 - 152
(2022/01/19)
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- Aryl C-F bond functionalization preparation method
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The invention relates to the technical field of organic compound synthesis, in particular to an aryl C-F bond functionalization preparation method. A fluorobenzene compound and a nucleophilic reagent react under the action of a composite catalyst, wherein the composite catalyst is formed by mixing a visible light catalyst and a metal catalyst. The photocatalyst is adopted, the reaction process is safe and controllable, and operation in the preparation and production process is simplified; a purple LED is used as a reaction energy source and is green and environment-friendly, the energy utilization rate is high, and conversion from light energy to chemical energy can be efficiently realized; in the reaction, a simple nucleophilic reagent is used for attacking free radical cation species generated under a visible light catalysis condition, so that a target product with an extremely wide range is efficiently and greenly prepared; the operation steps are simplified, and the reaction route is shortened; and moreover, the forward reaction rate is high, and the production efficiency is remarkably improved.
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Paragraph 0052; 0054-0057; 0081-0084
(2021/09/29)
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- MIDA boronate allylation-synthesis of ibuprofen
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MIDA boronates are among the most useful reagents for the Suzuki-Miyaura reaction. This chemistry typically generates new bonds between two aromatic rings, thereby restricting access to important areas of chemical space. Here we demonstrate the coupling of MIDA boronates to allylic electrophiles, including a new synthesis of the well-known COX inhibitor ibuprofen. This journal is
- Brodie, Glen,France, David J.,Memarzadeh, Sarah,Phillips, David,Tang, Gi Lum
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p. 30624 - 30630
(2020/09/11)
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- Palladium-Catalyzed Oxidative Allylation of Sulfoxonium Ylides: Regioselective Synthesis of Conjugated Dienones
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The first examples of palladium-catalyzed allylic C-H oxidative allylation of sulfoxonium ylides to afford the corresponding conjugated dienones with moderate to good yields have been established. The features of this novel conversion include mild reaction conditions, wide substrate scope, and excellent regioselectivity.
- Li, Chunsheng,Li, Meng,Zhong, Wentao,Jin, Yangbin,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
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supporting information
p. 872 - 875
(2019/05/16)
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- Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals
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In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.
- Wu, Fu-Peng,Li, Da,Peng, Jin-Bao,Wu, Xiao-Feng
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supporting information
p. 5699 - 5703
(2019/08/01)
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- Direct Alkenylation of Allylbenzenes via Chelation-Assisted C-C Bond Cleavage
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A novel method for direct transformation of allyl groups in allylbenzene derivatives to alkenyl groups via rhodium-catalyzed C-C bond cleavage is reported. The alkenylation with styrenes of allylbenzenes containing pyridyl and pyrazolyl groups as a directing group proceeded efficiently to give alkenylation products. We also developed a new protocol for transformation of an ortho-prenylated phenol to an aniline derivative.
- Onodera, Shunsuke,Ishikawa, Soya,Kochi, Takuya,Kakiuchi, Fumitoshi
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supporting information
p. 9788 - 9792
(2018/05/31)
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- Cross-Coupling Reactions of Aryldiazonium Salts with Allylsilanes under Merged Gold/Visible-Light Photoredox Catalysis
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A method for the cross-coupling reactions of aryldiazonium salts with trialkylallylsilanes via merged gold/photoredox catalysis is described. The reaction is proposed to proceed through a photoredox-promoted generation of an electrophilic arylgold(III) intermediate that undergoes transmetalation with allyltrimethylsilane to form allylarenes.
- Akram, Manjur O.,Mali, Pramod S.,Patil, Nitin T.
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supporting information
p. 3075 - 3078
(2017/06/23)
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- Catalytic Oxidative Trifluoromethoxylation of Allylic C?H Bonds Using a Palladium Catalyst
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A catalytic intermolecular allylic C?H trifluoromethoxylation reaction of alkenes has been developed based on the use of a palladium catalyst, CsOCF3 as the trifluoromethoxide source, and benzoquinone as the oxidant. This reaction provides an efficient route for directly accessing allylic trifluoromethoxy derivatives with excellent regioselectivities from terminal alkenes via an allylic C?H bond activation process.
- Qi, Xiaoxu,Chen, Pinhong,Liu, Guosheng
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supporting information
p. 9517 - 9521
(2017/08/01)
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- Anti-Markovnikov rearrangement in sulfur mediated allylic C-H amination of olefins
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Cationic rearrangement reactions usually follow Markovnikov's rule to give more substituted carbocations as stable intermediates. During our study on sulfur mediated allylic C-H amination of olefins, very rare cases of anti-Markovnikov rearrangement from secondary carbocations toward primary carbocations or primary triflates were observed.
- Zhang, Zhong,Du, Hongguang,Xu, Jiaxi,Li, Pingfan
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supporting information
p. 11547 - 11550
(2016/10/03)
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- Cascade multicomponent synthesis of indoles, pyrazoles, and pyridazinones by functionalization of alkenes
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The development of multicomponent reactions for indole synthesis is demanding and has hardly been explored. The present study describes the development of a novel multicomponent, cascade approach for indole synthesis. Various substituted indole derivative
- Matcha, Kiran,Antonchick, Andrey P.
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supporting information
p. 11960 - 11964
(2015/01/09)
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- (METH) ALLYLSILANE COMPOUND, SILANE COUPLING AGENT THEREFOR, AND FUNCTIONAL MATERIAL USING SAME
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Provided are: a (meth)allylsilane compound that is chemically bonded to various alcohol derivatives including polyol derivatives such as saccharides, is a raw material that is used to cause a substrate to express functionalities such as a defogging property and separation characteristics for column chromatography, can be easily prepared, is easily purified, and is stable and easy to handle, and a functional material in which those functionalities are expressed, while silyl group-containing groups are conveniently carried at a high density on the surface of the substrate, by using the (meth)allylsilane compound as a silane coupling agent for silane-coupling to the substrate. The (meth)allylsilane compound comprises a (meth)allylsilyl group-containing alkyl group or a (meth)allylsilylalkyl group-containing aralkyl group that is bonded to an alcohol derivative. In the functional material, the silane coupling agent is ether-bonded to surface hydroxyl groups exposed on a substrate through the surface hydroxyl groups by silane coupling to have an ether bond on the functional material.
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Paragraph 0060; 0061
(2014/05/20)
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- Method for Allylating and Vinylating Aryl, Heteroaryl, Alkyl, and Alkene Halogenides Using Transition Metal Catalysis
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What is described is a process for preparing organic compounds of the general formula (I) R—R′??(I) by converting a corresponding compound of the general formula (II) R—X ??(II) in which X is fluorine, chlorine, bromine or iodine to an organomagnesium compound of the general formula (III) [M+]n[RmMgXkY1]??(III) wherein compounds of the formula (III) are reacted with a compound of the general formula (IV) characterized in that the reaction of (III) with (IV) is performed in the presence of a) catalytic amounts of an iron compound, based on the compound of the general formula (II), and optionally in the presence of b) a nitrogen-, oxygen- and/or phosphorus-containing additive in a catalytic or stoichiometric amount, based on the compound of the general formula (II).
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Paragraph 0062; 0063; 0064
(2013/07/25)
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- A new synthetic approach for functional triisopropoxyorganosilanes using molecular building blocks
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We report an efficient synthetic approach for well-designed organic-bridged alkoxysilanes, which allow the formation of highly functional organosilica hybrids under mild sol-gel conditions. A series of molecular building blocks containing a triisopropoxys
- Maegawa, Yoshifumi,Waki, Minoru,Umemoto, Akinari,Shimada, Toyoshi,Inagaki, Shinji
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p. 5312 - 5318
(2013/06/27)
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- Cyclohexanones by Rh-mediated intramolecular C-H insertion
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Some long chain α-aryl α-diazo ketones under Rh catalysis cyclize efficiently to the corresponding cyclohexanones. This is in marked contrast to the cyclizations of α-diazo β-ketoesters, which consistently deliver cyclopentanone products.
- Taber, Douglass F.,Paquette, Craig M.,Gu, Peiming,Tian, Weiwei
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p. 9772 - 9780
(2013/10/22)
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- NOVEL THIOPHENE DERIVATIVES AS SPHINGOSINE-1-PHOSPHATE-1 RECEPTOR AGONISTS
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The invention relates to novel thiophene derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunosuppressive agents.
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- Carboxylation of alkylboranes by N-heterocyclic carbene copper catalysts: Synthesis of carboxylic acids from terminal alkenes and carbon dioxide
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Caught in the act: N-Heterocyclic carbene copper(I) complexes (1; IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) serve as an excellent catalyst for the carboxylation of alkylboranes (2; R=alkyl) with CO2 to afford a variety of functionalized carboxylic acids (3) in high yields. A novel copper methoxide/alkylborane adduct (A) and its subsequent CO2 insertion product (B) have been isolated and shown to be true active catalyst species.
- Ohishi, Takeshi,Zhang, Liang,Nishiura, Masayoshi,Hou, Zhaomin
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supporting information; experimental part
p. 8114 - 8117
(2011/10/18)
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- Synthesis of new cores and their use in the preparation of polyester dendrimers
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Six dendrimer and dendron cores terminated by hydroxyl groups that are neither phenolic nor cleavable by hydrogenolysis have been prepared in a consistent one-pot manner from terminal allyl groups by reduction of the product of reductive ozonolysis. Some of the terminal allyl derivatives are new and others have been prepared by new methods. The well-known O-benzylidene derivative of 2,2′-bis(hydroxymethyl)propanoic acid was shown to be the cis-stereoisomer. A new AB3-type anhydride, tris(benzyloxymethyl) acetic anhydride has been prepared. It was demonstrated that these cores and dendrons could be assembled into first and second generation homo- and mixed polyester dendrimers.
- Twibanire, Jean-D'Amour K.,Al-Mughaid, Hussein,Grindley, T. Bruce
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scheme or table
p. 9602 - 9609
(2011/01/03)
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- Novel Thiophene Derivatives as Spingosine-1-Phosphate-1 Receptor Agonists
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The invention relates to novel thiophene derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunosuppressive agents.
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Page/Page column 20
(2008/12/07)
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- Catalytic intermolecular allylic C-H alkylation
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The first electrophilic Pd(II)-catalyzed allylic C-H alkylation is reported, providing a novel method for formation of sp3-sp3 C-C bonds directly from C-H bonds. A wide range of aromatic and heteroaromatic linear (E)-α-nitro-arylpent
- Young, Andrew J.,White, M. Christina
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supporting information; experimental part
p. 14090 - 14091
(2009/03/11)
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- Novel Piperidine Carboxylic Acid Amide Derivatives
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The invention relates to novel piperidine carboxylic acid amide derivatives and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of these
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Page/Page column 8-9
(2008/12/08)
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- Rhodium-catalyzed intramolecular C-H insertion of α-aryl-α- diazo ketones
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(Chemical Equation Presented) Direct diazo transfer proceeds smoothly with α-aryl ketones. The derived α-aryl-α-diazo ketones cyclize efficiently with Rh catalysis to give the corresponding α-aryl cyclopentanones.
- Taber, Douglass F.,Tian, Weiwei
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p. 3207 - 3210
(2008/02/04)
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- Sodium dithionite initiated addition of 1-bromo-1-chloro-2,2,2-trifluoroethane to allylaromatics. Facile synthesis of conjugated dienes substituted with terminal CF3 group
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Sodium dithionite effectively promotes the addition of 1-bromo-1-chloro-2,2,2-trifluoroethane to the terminal double bond of allylbenzenes 1. The reactions proceeded in MeCN/H2O to give a 3:1 mole ratio of diastereoisomers of 1-(2-bromo-4-chloro-5,5,5-trifluoropentyl)benzenes 2 as the main products together with small amounts of its reductive debromination products 3. Total yields of 2 and 3 were dependent on the nature of the aromatic ring substituents in 1. Treatment of adducts 2 with DBU in refluxing hexanes resulted in double dehydrohalogenation affording, in good yields, conjugated dienes 4 (1,1,1-trifluoro-5-phenyl-2,4-pentadienes) terminated with the CF3 group at the one end and the phenyl group at the opposite end. These dienes were found to be sufficiently reactive to undergo Diels-Alder condensation with active dienophiles to give trifluoromethylated carbocycles. The reactions of CF3CHClBr with allylheterocycles were less successful and lead to low yields of mixtures of hardly separable compounds or to polymeric resins.
- Ignatowska, Jolanta,Dmowski, Wojciech
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p. 720 - 729
(2008/03/28)
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- Efficient synthesis of functionalized organozinc compounds by the direct insertion of zinc into organic iodides and bromides
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(Chemical Equation Presented) Insider dealing: A wide range of poly-functional (hetero)aromatic and aliphatic zinc reagents can be easily prepared in THF. The compounds are formed by a Zn insertion reaction mediated by the addition of LiCl (see scheme; All = allyl).
- Krasovskiy, Arkady,Malakhov, Vladimir,Gavryushin, Andrei,Knochel, Paul
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p. 6040 - 6044
(2007/10/03)
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- Synthesis of benzophenone-containing fatty acids
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(Chemical Equation Presented) Syntheses of new benzophenone-containing fatty acids (FABPs) 1, 5, and 6 and a new route to FABP 3 are described. Combined with the known 2 and 4, these FABPs comprise a set of photoactivatable fatty acid analogues with the crosslinking site at defined distances from the carboxylic acid hydroxyl group oxygen atoms ranging from 7.9 to 25.0 A.
- Gan, Yonghong,Wang, Pingzhen,Spencer, Thomas A.
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p. 9487 - 9490
(2007/10/03)
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- NOVEL DIAZABICYCLONONENE DERIVATIVE
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The invention relates to a novel 3,9-diazabicyclo[3.3.1]nonene derivative and the enantiomers thereof and the use thereof as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including proces
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Page/Page column 15
(2010/11/08)
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- (Sensitized) photolysis of diazonium salts as a mild general method for the generation of aryl cations. Chemoselectivity of the singlet and triplet 4-substituted phenyl cations
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(Chemical Equation Presented) The photolysis of a series of 4-X-benzenediazonium tetrafluoroborates is studied in MeCN. Loss of nitrogen occurs from the singlet excited state with X = H, t-Bu, and NMe2 and leads to the singlet aryl cation. This adds to the solvent yielding the corresponding acetanilides. With other substituents, ISC competes with (X = Br, CN) or overcomes (X = COMe, NO2) fragmentation and the aryl cation is formed in part or completely in the triplet state. In neat MeCN, this either abstracts hydrogen from the solvent (in most cases inefficiently) or undergoes intersystem crossing to the more stable singlet that reacts as above. In the presence of π nucleophiles (allyltrimethylsilane or benzene), the triplet aryl cation is efficiently trapped giving substituted allylbenzenes and biphenyls, respectively. By triplet sensitization by xanthone, the triplet cation and the products from it are obtained from the whole series considered. The direct or sensitized photodecomposition of diazonium fluoroborates, substituted with both electron-donating and -withdrawing substituents, in the presence of alkenes and arenes offers an access to an alternative arylation procedure.
- Milanesi, Silvia,Fagnoni, Maurizio,Albini, Angeld
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p. 603 - 610
(2007/10/03)
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- Method for producing Grignard compounds
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The invention relates to a process for preparing Grignard compounds of the formula I. The invention additionally relates to compounds of the formula I and to polymer-bound compounds of the formula Ia. The invention further relates to the use of the process for preparing substance libraries and to the use of the compounds of the formulae I and Ia in chemical synthesis.
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Page/Page column 11
(2008/06/13)
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- Preparation of para-terphenylylalkanethiols with different chain lengths
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Terphenylylalkanethiols with different chain length were synthesized using palladium-catalyzed cross-coupling reactions. While the thiols with two and three methylene groups were obtained via photoaddition of thiopivalic acid to the respective alkenes, the longer terphenylylalkanethiols were synthesized by two consecutive Kumada cross-coupling reactions followed by a Mitsunobu reaction for the introduction of the sulfur functionality. Georg Thieme Verlag Stuttgart.
- Mueller, Jan,Brunnbauer, Markus,Schmidt, Michael,Zimmermann, Anja,Terfort, Andreas
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p. 998 - 1004
(2007/10/03)
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- A highly effective (Triphenyl phosphite)palladium catalyst for a cross-coupling reaction of allylic alcohols with organoboronic acids
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The cross coupling reaction of aryl and vinyl boronic acids and allylic alcohols proceeded smoothly in toluene or dioxane in the presence of a (triphenyl phosphite)palladium catalyst to give the corresponding allylbenzene derivatives and 1,4-dienes. Neither cocatalysts for promoting C-O bond cleavage of allylic alcohols nor bases for activation of organoboron reagents are required for promoting the coupling process. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Kayaki, Yoshihito,Koda, Takashi,Ikariya, Takao
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p. 4989 - 4993
(2007/10/03)
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- Efficient and selective Stille cross-coupling of benzylic and allylic bromides using bromobis(triphenylphosphine)(N-succinimide)palladium(II)
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Allylic and benzylic bromides are cross-coupled with organostannanes efficiently using the precatalyst [Pd(NCOC2H4CO)(PPh 3)2Br] 1. Significantly, these reactions do not require the use of hexamethylphosphoramide (HMPA) as the solvent, or additional ligands, such as trifurylphosphine or triphenylarsine. Selectivity for benzyl bromide over bromobenzene is observed for precatalyst 1, against the precatalysts, bromobis(triphenylphosphine)(benzyl)palladium(II) and bis(triphenylphosphine) palladium(II) bromide.
- Crawforth, Catherine M.,Fairlamb, Ian J. S.,Taylor, Richard J. K.
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p. 461 - 465
(2007/10/03)
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- Aromatic allylation via diazotization: Metal-free C-C bond formation
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A new method for the synthesis of allyl aromatic compounds not involving any metal-containing reagent or catalyst has been developed. Arylamines substituted with a large number of different substituents were converted via diazotizative deamination with tert-butyl nitrite in allyl bromide and acetonitrile to the corresponding allyl aromatic compounds. The allylation reaction was found to be suitable for larger scale synthesis due to short reaction times, a nonextractive workup, and robustness toward moisture, air, and type of solvent.
- Ek, Fredrik,Axelsson, Oskar,Wistrand, Lars-Goeran,Frejd, Torbjoern
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p. 6376 - 6381
(2007/10/03)
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- Preparation of allylic aromatic compounds
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A process for the preparation of an allylic aromatic compound in which an aromatic amine is reacted first with a nitrite and then with an allylic olefin having an eliminatable terminal substituent. Novel allylic derivatives of disubstituted benzene compou
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- Halogen-magnesium exchange via trialkylmagnesates for the preparation of aryl- and alkenymagnesium reagents
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Significantly better than simple Grignard reagents are the trialkylmagnesium-ate complexes in the halogen-metal exchange reaction of aryl or alkenyl halides to the corresponding magnesates (see reaction scheme). The subsequent reaction of these ate complexes with electrophiles proceeds in good to excellent yields, and a number of functional groups (FG) can be tolerated.
- Kitagawa, Kazuya,Inoue, Atsushi,Shinokubo, Hiroshi,Oshima, Koichiro
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p. 2481 - 2483
(2007/10/03)
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- Modular Construction of Dendritic Carbosilanes. Organization of Dendrimer Connectivity around Bifunctional Precursors That Are Adapted for Sequential Convergent and Divergent Propagative Steps
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(Matrix Presented) Rdend = -CH2(CH2)2Si(Me)[CH2(CH 2)2Si(Me)(CH2CH=CH2) 2]2 Regiospecific hydrosilylation of 1-bromo-4-(prop-2-enyl)benzene offers an efficient route to molecular building block precursors that can accommodate sequential divergent and convergent steps for dendritic extension, establishing a modular methodology for assembly and organization of connectivity used for synthesis of modified carbosilane dendrimers including 14.
- Casado, Miguel Angel,Stobart, Stephen R.
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p. 1549 - 1552
(2007/10/03)
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- Preparation of highly functionalized Grignard reagents by an iodine-magnesium exchange reaction and its application in solid-phase synthesis
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At -40°C aryl iodides that contain other functional groups can be selectively converted into Grignard reagents, which react with electrophiles such as benzaldehyde in the usual manner [Eq. (a)]. Aryl bromides and iodides that are immobilized as esters on a Wang resin behave analogously.
- Boymond, Laure,Rottlaender, Mario,Cahiez, Gerard,Knochel, Paul
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p. 1701 - 1703
(2007/10/03)
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- Nickel catalyzed tellurium-zinc exchange reactions. A new preparation of arylzinc reagents
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Diaryltellurides 2 and diarylditellurides 3 undergo a smooth tellurium-zine exchange reaction in the presence of catalytic amounts of Ni(acac)2 (5-10 mmol %) leading to arylzinc derivatives 1. The reaction can be extended to the preparation of alkylzinc compounds and allows a stereoselective cyclization to a 2,4-disubstituted tetrahydrofuran by a radical ring closure of an unsaturated telluride.
- Stuedemann, Thomas,Gupta, Vijay,Engman, Lars,Knochel, Paul
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p. 1005 - 1008
(2007/10/03)
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- Substituted aromatic silane compounds and method for preparation of same
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A new group of silane compounds in which silicon atoms are linked together by a hydrocarbon chain and which comprise phenyl groups substituted with an epoxy group or an ethenyl group. The compounds of the present invention have the formula STR1 where Rsu
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- Preparation and Properties of Tertiary p-Alkylarylphosphines containing Straight-chain Alkyl Groups
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A series of tris(p-alkylaryl)phosphines with straight-chain alkyl groups, P(p-C6H4-CnH2n+1)3 where n=2-9, have been prepared by reaction of phosphorus trichloride with the Grignard reagent derived from the corresponding p-bromoalkylbenzene.When n=2 and 3 the phosphines are crystalline solids, but for n>3 they are viscous oils up to n=9, which is a waxy solid.The phosphines have been characterised by microanalysis, and i.r., 1H and 31P n.m.r., and mass spectrometry.The p-substituted-arylphosphines are more sensitive than triphenylphosphine to air; aerial oxidation converts them exclusively into the corresponding phosphine oxides, in contrast to trialkylphosphines which are oxidised to a complex mixture of products.The complexing ability of the new phosphines (PAr3) is demonstrated by their ready displacement of 1,5-cyclo-octadiene (cod) from (M=Pd and Pt) to yield trans- and cis-, respectively.
- Franks, Stephen,Hartley, Frank R.
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p. 2233 - 2237
(2007/10/02)
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